After trying what Jim Travis said, it could be the Fuel pressure regulator (FPR) the first couple years of these beasts are more commonly having this issue, as the little diaphragms in them dry out and crack, a factor of old age, not overuse or misuse. This condition allows fuel to leak into the cylinders and into the crankcase. Located just under the left side of the fuel tank between the jugs, held in place by 2 small bolts, with a couple hoses coming off. $40, + or -, will get you a new one. A telltale sign it's going bad is a strong fuel smell in your oil, or an over-full reading on the dipstick. Don't ride like this- no lube for the bearings. Change the FPR, change your oil filter and oil, using a cheap brand to flush out the contaminants. Run it around the block, then change just the oil a 2nd time using whatever good oil you prefer. Let us know what you find.
You're right, if it's running really rich, possibly the FPR, but that does not at all explain the cutting out. A failed FPR won't have the bike cutting out on the freeway.
Based on what he's described, I would point in the direction of the PCIII.